N-phenyl-imidazolidine-1-ones

Abstract

Compounds of the formula ##SPC1## Wherein R is hydrogen, halogen, lower alkyl or lower alkoxy, R' is --CHR 1 --Q--A, --CHR 2 --A or --O--CHR 2 --CHR 1 --Q--A, each in m- or p-position, Where A is ##SPC2## Q is straight or branched alkylene of 1 to 4 carbon atoms, R 1 is hydrogen, hydroxyl, lower alkoxy or --O--CO--R 5 , R 2 is hydrogen or methyl, R 3 and R 4 , which may be identical to or different from each other, are each hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl or, together with each other and neighboring carbon atoms of the phenyl ring to which they are attached, form a saturated or unsaturated carbocyclic 5- to 6-membered ring, R 5 is lower alkyl, halo-lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, amino, (mono-lower alkyl)-amino or (di-lower alkyl)-amino, Z is an aromatic heterocyclic ring with one to two heteroatoms, which may optionally be condensed with a benzene ring, and R" is hydrogen, straight or branched lower alkyl, lower alkenyl, lower alkynyl, hydroxy-lower alkyl, (di-lower alkyl)-amino-lower alkyl or aralkyl, And their non-toxic, pharmacologically acceptable acid addition salts; the compounds as well as their salts are useful as CNS-depressants, neuroleptics, analgesics, antiphlogistics, spasmolytics, broncholytics, hypotensives and anti-cholesteremics.

We claim: 
     
       1. A compound of the formula ##SPC60## wherein   R' is in the m- or p- position and is selected from the group consisting of --CH 2  --A, --CHR 1  --CH 2  -A and ##EQU3## where R 1  is hydrogen or hydroxyl, and A is ##SPC61##   where R 3  is hydrogen, chlorine, methyl, ethyl, trifluoromethyl or lower alkoxy, and   R 4  is hydrogen or methyl, or   R 3  and R 4 , together with each other and neighboring carbon atoms of the phenyl ring to which they are attached, are naphthyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.         
     
     
       2. A compound of claim 1, wherein R' is in the m- or p- position and is selected from the group consisting of --CH 2  --A, --CHR 1  --CH 2  -A and ##EQU4## where R 1  is hydrogen or hydroxyl, and A is ##SPC62##   where R 3  is hydrogen, chlorine, methyl or ethyl, and   R 4  is hydrogen or methyl, or   R 3  and R 4 , together with each other and neighboring carbon atoms of the phenyl ring to which they are attached, are naphthyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.         
     
     
       3. A compound of claim 2 wherein R' is in the m- or p- position and is selected from the group consisting of --CH 2  --CH 2  --A and ##EQU5## where A is ##SPC63## where R 3  is hydrogen, chlorine, methyl or ethyl, and   R 4  is hydrogen or methyl, or   R 3  and R 4 , together with each other and neighboring carbon atoms of the phenyl ring to which they are attached, are naphthyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.         
     
     
       4. A compound of claim 1, which is N-[4"-imidazolidinon-(2')-yl-phenethyl]-N' -(o-ethyl-phenyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof. 
     
     
       5. A compound of claim 1, which is N-[4"-imidazolidinon-(2')-yl-phenethyl]-N'-(o-methyl-phenyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.